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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (10) Show 10 proteins XML

enzymes (10) Show 10 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-07 16:24:12 UTC

HMDB ID

HMDB0000224

Secondary Accession Numbers

HMDB0012279
HMDB00224
HMDB0060151
HMDB0060152
HMDB12279
HMDB60151
HMDB60152

Metabolite Identification

Common Name

O-Phosphoethanolamine

Description

O-Phosphoethanolamine, also known as PEA, phosphorylethanolamine, colamine phosphoric acid or ethanolamine O-phosphate, belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. O-Phosphoethanolamine is used in the biosynthesis of two different types of phospholipids: glycerophospholipids and sphingolipids. O-Phosphoethanolamine exists in all living species, ranging from bacteria to plants to humans. Within humans, O-phosphoethanolamine participates in a number of enzymatic reactions. In particular, cytidine triphosphate and O-phosphoethanolamine can be converted into CDP-ethanolamine; which is mediated by the enzyme ethanolamine-phosphate cytidylyltransferase. In addition, O-phosphoethanolamine can be biosynthesized from ethanolamine; which is catalyzed by the enzyme choline/ethanolamine kinase. In humans, O-phosphoethanolamine is involved in phosphatidylcholine biosynthesis. O-phosphoethanolamine is also a product of the metabolism of sphingolipids. In particular, sphinglipids are metabolized in vivo to phosphorylethanolamine and a fatty aldehyde, generally palmitaldehyde. Both metabolites are ultimately converted to glycerophospholipids. The lipids are first phosphorylated by a kinase and then cleaved by the pyridoxal-dependent sphinganine-1-phosphate aldolase. Elevated urine levels of O-Phosphoethanolamine or PEA can be used to help in the diagnosis of Hypophosphatasia (HPP). Reference ranges for urinary PEA vary according to age and somewhat by diet, and follow a circadian rhythm. Outside of the human body, O-phosphoethanolamine has been detected, but not quantified in, several different foods, such as oxheart cabbages, anises, shiitakes, abalones, and teffs.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Amino-ethanol dihydrogen phosphate	ChEBI
2-Amino-ethanol phosphate	ChEBI
Colamine phosphate	ChEBI
Colamine phosphoric acid	ChEBI
Colaminphosphoric acid	ChEBI
EAP	ChEBI
Ethanolamine acid phosphate	ChEBI
Ethanolamine O-phosphate	ChEBI
Ethanolamine phosphate	ChEBI
mono(2-Aminoethyl) phosphate	ChEBI
Monoaminoethyl phosphate	ChEBI
O-Phosphocolamine	ChEBI
O-Phosphorylethanolamine	ChEBI
OPE	ChEBI
PE	ChEBI
PEA	ChEBI
PETN	ChEBI
Phosphoethanolamine	ChEBI
Phosphoric acid 2-aminoethyl phenyl ester	ChEBI
Phosphoryl-ethanolamine	ChEBI
2-Amino-ethanol dihydrogen phosphoric acid	Generator
2-Amino-ethanol phosphoric acid	Generator
Colaminphosphate	Generator
Ethanolamine acid phosphoric acid	Generator
Ethanolamine O-phosphoric acid	Generator
Ethanolamine phosphoric acid	Generator
mono(2-Aminoethyl) phosphoric acid	Generator
Monoaminoethyl phosphoric acid	Generator
Phosphate 2-aminoethyl phenyl ester	Generator
Phosphonoethanolamine	HMDB
2-Amino-ethanol dihydrogen phosphate (ester)	HMDB
2-Aminoethanol O-phosphate	HMDB
2-Aminoethyl dihydrogen phosphate	HMDB
2-Aminoethyl dihydrogen phosphate (acd/name 4.0)	HMDB
2-Aminoethyl phosphate	HMDB
Colamine acid phosphate	HMDB
Colaminephosphoric acid	HMDB
Ethamp	HMDB
O-Phosphonatoethanaminium	HMDB
Phosphoryethanolamine	HMDB
Phosphorylethanolamine	HMDB
Phosphorylethanolamine, 3H-labeled CPD	HMDB
Phosphorylethanolamine magnesium (1:1) salt	HMDB
Phosphorylethanolamine zinc salt	HMDB
Phosphorylethanolamine, cobalt (2+) (1:1) salt	HMDB
Calcium 2-aminoethanol phosphate	HMDB
Phosphorylethanolamine ca (1:1) salt	HMDB

Chemical Formula

C₂H₈NO₄P

Average Molecular Weight

141.063

Monoisotopic Molecular Weight

141.019094261

IUPAC Name

(2-aminoethoxy)phosphonic acid

Traditional Name

phosphorylethanolamine

CAS Registry Number

1071-23-4

SMILES

NCCOP(O)(O)=O

InChI Identifier

InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)

InChI Key

SUHOOTKUPISOBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Phosphoethanolamines

Alternative Parents

Substituents

Phosphoethanolamine
Monoalkyl phosphate
Alkyl phosphate
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary amino compound (CHEBI:17553 )
phosphoethanolamine (CHEBI:17553 )

Ontology

Physiological effect

Adverse health effect

Genetic disorder

Inborn errors of metabolism

Digestive system disorder

Gastrointestinal disorder

Upper GI Disorder

Eosinophilic esophagitis (PMID: 17334708 , PMID: 32966057 , PMID: 22623390 , +128

Source	Link
Pubmed	PMID: 17334708
Pubmed	PMID: 32966057
Pubmed	PMID: 22623390
Pubmed	PMID: 16870009
Pubmed	PMID: 26910390
Pubmed	PMID: 8087979
Pubmed	PMID: 25105552
Pubmed	PMID: 17349089
Pubmed	PMID: 24023812
Pubmed	PMID: 12376931
Pubmed	PMID: 15992788
Pubmed	PMID: 24341803
Pubmed	PMID: 19468821
Pubmed	PMID: 9625050
Pubmed	PMID: 2420598
Pubmed	PMID: 27012787
Pubmed	PMID: 30830347
Pubmed	PMID: 19551947
Pubmed	PMID: 19309105
Pubmed	PMID: 2026685
Pubmed	PMID: 5727921
Pubmed	PMID: 22024767
Pubmed	PMID: 17031479
Pubmed	PMID: 9439441
Pubmed	PMID: 9625050
Pubmed	PMID: 28649521
Pubmed	PMID: 28649521
Pubmed	PMID: 12097436
Pubmed	PMID: 8257730
Pubmed	PMID: 3168222
Pubmed	PMID: 9869364
Pubmed	PMID: 3436096
Pubmed	PMID: 22157537
Pubmed	PMID: 1246461
Pubmed	PMID: 25691415
Pubmed	PMID: 18004736
Pubmed	PMID: 31506554
Pubmed	PMID: 20423563
Pubmed	PMID: 25536744
Pubmed	PMID: 21388201
Pubmed	PMID: 4903899
Pubmed	PMID: 14708889
Pubmed	PMID: 14967154
Pubmed	PMID: 6774165
Pubmed	PMID: 21389975
Pubmed	PMID: 3709568
Pubmed	PMID: 8311084
Pubmed	PMID: 2242313
Pubmed	PMID: 20549362
Pubmed	PMID: 12555941
Pubmed	PMID: 10731506
Pubmed	PMID: 28157703
Pubmed	PMID: 20576202
Pubmed	PMID: 12368406
Pubmed	PMID: 26066683
Pubmed	PMID: 16736096
Pubmed	PMID: 25597510
Pubmed	PMID: 22800120
Pubmed	PMID: 16139832
Pubmed	PMID: 17287286
Pubmed	PMID: 17301081
Pubmed	PMID: 30817767
Pubmed	PMID: 25851806
Pubmed	PMID: 2587127
Pubmed	PMID: 11893004
Pubmed	PMID: 10102904
Pubmed	PMID: 23430553
Pubmed	PMID: 12705346
Pubmed	PMID: 19075476
Pubmed	PMID: 3571488
Pubmed	PMID: 7776094
Pubmed	PMID: 31963255
Pubmed	PMID: 23093139
Pubmed	PMID: 22284503
Pubmed	PMID: 8503438
Pubmed	PMID: 1246461
Pubmed	PMID: 20502474
Pubmed	PMID: 15558695
Pubmed	PMID: 422265
Pubmed	PMID: 22308371
Pubmed	PMID: 20549362
Pubmed	PMID: 9177981
Pubmed	PMID: 16828325
Pubmed	PMID: 16460720
Pubmed	PMID: 28157703
Pubmed	PMID: 8487492
Pubmed	PMID: 23890588
Pubmed	PMID: 14586528
Pubmed	PMID: 12927681
Pubmed	PMID: 9686366
Pubmed	PMID: 9029640
Pubmed	PMID: 22148915
Pubmed	PMID: 27123458
Pubmed	PMID: 20971021
Pubmed	PMID: 3169394
Pubmed	PMID: 21670092
Pubmed	PMID: 23363473
Pubmed	PMID: 15519880
Pubmed	PMID: 2380628
Pubmed	PMID: 6616873
Pubmed	PMID: 1870421
Pubmed	PMID: 19754154
Pubmed	PMID: 9857238
Pubmed	PMID: 12771321
Pubmed	PMID: 2702744
Pubmed	PMID: 9554495
Pubmed	PMID: 19033659
Pubmed	PMID: 19033659
Pubmed	PMID: 22887155
Pubmed	PMID: 17474139
Pubmed	PMID: 18953024
Pubmed	PMID: 6774165
Pubmed	PMID: 11052553
Pubmed	PMID: 16939360
Pubmed	PMID: 22827565
Pubmed	PMID: 21736852
Pubmed	PMID: 12661026
Pubmed	PMID: 18818040
Pubmed	PMID: 23770102
Pubmed	PMID: 15651030
Pubmed	PMID: 11307586
Pubmed	PMID: 21389975
Pubmed	PMID: 1640293
Pubmed	PMID: 25712379
Pubmed	PMID: 23770102
Pubmed	PMID: 24390407
Pubmed	PMID: 26709303
Pubmed	PMID: 3354621
Pubmed	PMID: 29030856
Pubmed	PMID: 12706375
Pubmed	PMID: 9869358

)

Disposition

Biological location

Cellular substructure

Cytoplasm

Organelle

Endoplasmic reticulum

Non-excretory biofluid

Blood
Saliva

Excreta

Feces
Urine

Organ

Placenta

Green lentil

Other pulses

Peas

Lentils

Lentils

Onion-family vegetables

Herb and spice mixtures

Curry powder

Cereals and cereal products

Cereals

Cereal products

Doughs

Sourdough

Leavened breads

Flat breads

Other breads

Potato bread

Sweet breads

Raisin bread

Teas

Herbal tea

Herbal teas

Taco shell
Tostada shell

Nuts

Cocoa and cocoa products

Cocoa

Cocoa bean

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Coffee and coffee products

Coffee

Milk and milk products

Unfermented milks

Milk (Cow)

Soy

Soy products

Soy bean

Baking goods

Wrappers

Wonton wrapper

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	241 - 243 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	72 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	121.596	30932474
[M-H]-	Not Available	123.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000011

Predicted Molecular Properties

Property	Value	Source
Water Solubility	25.8 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-2.5	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	1.54	ChemAxon
pKa (Strongest Basic)	10.02	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	27.08 m³·mol⁻¹	ChemAxon
Polarizability	11.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.62	31661259
DarkChem	[M-H]-	121.624	31661259
AllCCS	[M+H]+	132.883	32859911
AllCCS	[M-H]-	127.361	32859911
DeepCCS	[M+H]+	127.669	30932474
DeepCCS	[M-H]-	124.87	30932474
DeepCCS	[M-2H]-	161.286	30932474
DeepCCS	[M+Na]+	135.812	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Phosphoethanolamine	NCCOP(O)(O)=O	2065.2	Standard polar	33892256
O-Phosphoethanolamine	NCCOP(O)(O)=O	1369.0	Standard non polar	33892256
O-Phosphoethanolamine	NCCOP(O)(O)=O	1428.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Phosphoethanolamine,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OCCN	1444.3	Semi standard non polar	33892256
O-Phosphoethanolamine,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OCCN	1352.1	Standard non polar	33892256
O-Phosphoethanolamine,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OCCN	2301.6	Standard polar	33892256
O-Phosphoethanolamine,1TMS,isomer #2	C[Si](C)(C)NCCOP(=O)(O)O	1553.1	Semi standard non polar	33892256
O-Phosphoethanolamine,1TMS,isomer #2	C[Si](C)(C)NCCOP(=O)(O)O	1437.8	Standard non polar	33892256
O-Phosphoethanolamine,1TMS,isomer #2	C[Si](C)(C)NCCOP(=O)(O)O	2505.0	Standard polar	33892256
O-Phosphoethanolamine,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OCCN)O[Si](C)(C)C	1457.0	Semi standard non polar	33892256
O-Phosphoethanolamine,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OCCN)O[Si](C)(C)C	1452.6	Standard non polar	33892256
O-Phosphoethanolamine,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OCCN)O[Si](C)(C)C	1924.0	Standard polar	33892256
O-Phosphoethanolamine,2TMS,isomer #2	C[Si](C)(C)NCCOP(=O)(O)O[Si](C)(C)C	1565.4	Semi standard non polar	33892256
O-Phosphoethanolamine,2TMS,isomer #2	C[Si](C)(C)NCCOP(=O)(O)O[Si](C)(C)C	1550.1	Standard non polar	33892256
O-Phosphoethanolamine,2TMS,isomer #2	C[Si](C)(C)NCCOP(=O)(O)O[Si](C)(C)C	1960.5	Standard polar	33892256
O-Phosphoethanolamine,2TMS,isomer #3	C[Si](C)(C)N(CCOP(=O)(O)O)[Si](C)(C)C	1736.4	Semi standard non polar	33892256
O-Phosphoethanolamine,2TMS,isomer #3	C[Si](C)(C)N(CCOP(=O)(O)O)[Si](C)(C)C	1657.1	Standard non polar	33892256
O-Phosphoethanolamine,2TMS,isomer #3	C[Si](C)(C)N(CCOP(=O)(O)O)[Si](C)(C)C	2391.9	Standard polar	33892256
O-Phosphoethanolamine,3TMS,isomer #1	C[Si](C)(C)NCCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1591.7	Semi standard non polar	33892256
O-Phosphoethanolamine,3TMS,isomer #1	C[Si](C)(C)NCCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1635.6	Standard non polar	33892256
O-Phosphoethanolamine,3TMS,isomer #1	C[Si](C)(C)NCCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1676.1	Standard polar	33892256
O-Phosphoethanolamine,3TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C	1751.0	Semi standard non polar	33892256
O-Phosphoethanolamine,3TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C	1730.0	Standard non polar	33892256
O-Phosphoethanolamine,3TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C	1919.3	Standard polar	33892256
O-Phosphoethanolamine,4TMS,isomer #1	C[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1773.0	Semi standard non polar	33892256
O-Phosphoethanolamine,4TMS,isomer #1	C[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1771.1	Standard non polar	33892256
O-Phosphoethanolamine,4TMS,isomer #1	C[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1708.5	Standard polar	33892256
O-Phosphoethanolamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OCCN	1680.4	Semi standard non polar	33892256
O-Phosphoethanolamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OCCN	1557.0	Standard non polar	33892256
O-Phosphoethanolamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OCCN	2374.9	Standard polar	33892256
O-Phosphoethanolamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCOP(=O)(O)O	1791.8	Semi standard non polar	33892256
O-Phosphoethanolamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCOP(=O)(O)O	1654.2	Standard non polar	33892256
O-Phosphoethanolamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCOP(=O)(O)O	2611.2	Standard polar	33892256
O-Phosphoethanolamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCCN)O[Si](C)(C)C(C)(C)C	1910.7	Semi standard non polar	33892256
O-Phosphoethanolamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCCN)O[Si](C)(C)C(C)(C)C	1852.8	Standard non polar	33892256
O-Phosphoethanolamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCCN)O[Si](C)(C)C(C)(C)C	2068.7	Standard polar	33892256
O-Phosphoethanolamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCOP(=O)(O)O[Si](C)(C)C(C)(C)C	1996.9	Semi standard non polar	33892256
O-Phosphoethanolamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCOP(=O)(O)O[Si](C)(C)C(C)(C)C	1991.4	Standard non polar	33892256
O-Phosphoethanolamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCOP(=O)(O)O[Si](C)(C)C(C)(C)C	2182.2	Standard polar	33892256
O-Phosphoethanolamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCOP(=O)(O)O)[Si](C)(C)C(C)(C)C	2128.3	Semi standard non polar	33892256
O-Phosphoethanolamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCOP(=O)(O)O)[Si](C)(C)C(C)(C)C	2071.8	Standard non polar	33892256
O-Phosphoethanolamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCOP(=O)(O)O)[Si](C)(C)C(C)(C)C	2485.1	Standard polar	33892256
O-Phosphoethanolamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2224.0	Semi standard non polar	33892256
O-Phosphoethanolamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2205.0	Standard non polar	33892256
O-Phosphoethanolamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2045.2	Standard polar	33892256
O-Phosphoethanolamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2379.9	Semi standard non polar	33892256
O-Phosphoethanolamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2327.9	Standard non polar	33892256
O-Phosphoethanolamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2216.7	Standard polar	33892256
O-Phosphoethanolamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2601.2	Semi standard non polar	33892256
O-Phosphoethanolamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2483.1	Standard non polar	33892256
O-Phosphoethanolamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2130.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - O-Phosphoethanolamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0fki-0910000000-63541b89e6730018e48b	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - O-Phosphoethanolamine GC-MS (4 TMS)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - O-Phosphoethanolamine GC-EI-TOF (Non-derivatized)	splash10-0fki-0910000000-63541b89e6730018e48b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - O-Phosphoethanolamine GC-MS (Non-derivatized)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - O-Phosphoethanolamine GC-MS (Non-derivatized)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - O-Phosphoethanolamine GC-MS (Non-derivatized)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - O-Phosphoethanolamine GC-EI-TOF (Non-derivatized)	splash10-0fki-0911000000-7fc066f17e2ebf6c84f8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Phosphoethanolamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-9100000000-543d2d90aa663406e999	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Phosphoethanolamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-88dc3b66f275af50de34	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0006-2900000000-9cf72ee86018eb78504f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-004i-9000000000-169b03f94a9f53bd0de4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-004i-9000000000-199d7ab7a4aeb040674e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-004i-9000000000-f573b62dada3630598c3	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-004i-9000000000-38c04ce07a85a8db342c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-004i-9100000000-b582c6b51602884756da	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ , negative-QTOF	splash10-0006-2900000000-9cf72ee86018eb78504f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-169b03f94a9f53bd0de4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-199d7ab7a4aeb040674e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-f573b62dada3630598c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-38c04ce07a85a8db342c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QTOF , negative-QTOF	splash10-004i-9100000000-b582c6b51602884756da	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine , negative-QTOF	splash10-004i-9000000000-4335e927ba2537543f7d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine , negative-QTOF	splash10-004i-9000000000-3e5f10c6e140e555b9fe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine 40V, Negative-QTOF	splash10-004i-9000000000-db65ce46b55b09e54fd2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine 20V, Negative-QTOF	splash10-004i-9000000000-2fd2f3cd8548fd78801d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine 10V, Negative-QTOF	splash10-004i-9000000000-f56d20ee0f56f087220d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine 35V, Negative-QTOF	splash10-004i-9000000000-d64f2b030ca512262fb1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0006-9100000000-993b8efd11624567ec4b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-9000000000-f2fd3c258685af07afb5	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9000000000-b479823e7c0ee6b5e03d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine 40V, Positive-QTOF	splash10-0006-9000000000-c4e1a40502d86192ed6b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine 10V, Positive-QTOF	splash10-0006-9000000000-b5f55e00526c703b9bed	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine 20V, Positive-QTOF	splash10-0006-9000000000-e5987c09032f652371ca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Phosphoethanolamine 10V, Positive-QTOF	splash10-0006-9000000000-42653da62fb10227ae1b	2021-09-20	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Starch and sucrose metabolism	Not Available
Gaucher Disease		Not Available
Globoid Cell Leukodystrophy		Not Available
Metachromatic Leukodystrophy (MLD)		Not Available
Fabry disease		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	19 +/- 9.9 uM	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	4.0 +/- 2.0 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	6.0 +/- 1.1 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	6.30 (4.70-9.60) uM	Adult (>18 years old)	Both	Normal	15756940	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected and Quantified	50.9 +/- 34.1 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	66.2 +/- 20.4 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	76.2 +/- 64.8 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	12097436	details
Saliva	Detected and Quantified	14.8 +/- 17.4 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Urine	Detected and Quantified	30.53 +/- 32.79 umol/mmol creatinine	Newborn (0-30 days old)	Not Specified	Normal	19468821	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	<9.95 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	0-53 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	23093084	details
Urine	Detected and Quantified	142.263 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	<5.43 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	1.69-38.57 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	3.73-38.69 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	4.276 (1.644-6.908) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Not Available	details
Urine	Detected and Quantified	2.15-18.55 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	8.2 +/- 2.0 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	<25 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	23093139	details
Urine	Detected and Quantified	1.36-13.35 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	7.91 +/- 18.09 umol/mmol creatinine	Newborn (0-30 days old)	Not Specified	Normal	19468821	details
Urine	Detected and Quantified	10.18 +/- 12.44 umol/mmol creatinine	Newborn (0-30 days old)	Not Specified	Normal	19468821	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.3 (6.50-16.4) uM	Adult (>18 years old)	Both	Brain injury	15756940	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Urine	Detected and Quantified	71.48 +/- 35.869 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	84 umol/mmol creatinine	Children (1-13 years old)	Female	Odontohypophosphatasia	23093139	details

Associated Disorders and Diseases

Disease References

Traumatic brain injury
Seki Y, Kimura M, Mizutani N, Fujita M, Aimi Y, Suzuki Y: Cerebrospinal fluid taurine after traumatic brain injury. Neurochem Res. 2005 Jan;30(1):123-8. [PubMed:15756940 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Odontohypophosphatasia
Haliloglu B, Guran T, Atay Z, Abali S, Mornet E, Bereket A, Turan S: Infantile loss of teeth: odontohypophosphatasia or childhood hypophosphatasia. Eur J Pediatr. 2013 Jun;172(6):851-3. doi: 10.1007/s00431-012-1868-4. Epub 2012 Oct 24. [PubMed:23093139 ]

Associated OMIM IDs

266600 (Crohn's disease)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)
146300 (Odontohypophosphatasia)

External Links

DrugBank ID

DB01738

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031115

KNApSAcK ID

Not Available

Chemspider ID

990

KEGG Compound ID

C00346

BioCyc ID

PHOSPHORYL-ETHANOLAMINE

BiGG ID

1485304

Wikipedia Link

Phosphorylethanolamine

METLIN ID

5233

PubChem Compound

1015

PDB ID

Not Available

ChEBI ID

17553

Food Biomarker Ontology

Not Available

VMH ID

ETHAMP

MarkerDB ID

MDB00000106

Good Scents ID

Not Available

References

Synthesis Reference

Muller K; Schulz J; Oemus R Phosphoethanolamine--a substrate of alkaline phosphatase isolated from rat calvaria. Biomedica biochimica acta (1989), 48(8), 495-504.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
Seki Y, Kimura M, Mizutani N, Fujita M, Aimi Y, Suzuki Y: Cerebrospinal fluid taurine after traumatic brain injury. Neurochem Res. 2005 Jan;30(1):123-8. [PubMed:15756940 ]
Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
Klunk WE, Debnath ML, McClure RJ, Pettegrew JW: Inactivity of phosphoethanolamine, an endogenous GABA analog decreased in Alzheimer's disease, at GABA binding sites. Life Sci. 1995;56(26):2377-83. [PubMed:7791524 ]
Klunk WE, McClure RJ, Xu CJ, Pettegrew JW: Structural determinants of activity at the GABAB receptor. A comparison of phosphoethanolamine and related GABA analogs. Mol Chem Neuropathol. 1995 Sep;26(1):15-30. [PubMed:8588821 ]
Li G, Foote C, Alexander S, Alexander H: Sphingosine-1-phosphate lyase has a central role in the development of Dictyostelium discoideum. Development. 2001 Sep;128(18):3473-83. [PubMed:11566853 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Ethanolamine-phosphate cytidylyltransferase

General function:: Involved in catalytic activity
Specific function:: Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine.
Gene Name:: PCYT2
Uniprot ID:: Q99447
Molecular weight:: 35199.52

Reactions

Cytidine triphosphate + O-Phosphoethanolamine → Pyrophosphate + CDP-ethanolamine	details

Enzyme Details

2. Choline/ethanolamine kinase

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Has a key role in phospholipid biosynthesis. Catalyzes the first step in phosphatidylethanolamine biosynthesis. Phosphorylates ethanolamine, and can also act on choline (in vitro). Has higher activity with ethanolamine. May not significantly contribute to in vivo phosphatidylcholine biosynthesis.
Gene Name:: CHKB
Uniprot ID:: Q9Y259
Molecular weight:: 45270.99

Reactions

Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolamine	details

Enzyme Details

3. Choline kinase alpha

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Has a key role in phospholipid biosynthesis and may contribute to tumor cell growth. Catalyzes the first step in phosphatidylcholine biosynthesis. Contributes to phosphatidylethanolamine biosynthesis. Phosphorylates choline and ethanolamine. Has higher activity with choline.
Gene Name:: CHKA
Uniprot ID:: P35790
Molecular weight:: 52248.53

Reactions

Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolamine	details

Enzyme Details

4. Ethanolamine kinase 1

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Highly specific for ethanolamine phosphorylation. May be a rate-controlling step in phosphatidylethanolamine biosynthesis.
Gene Name:: ETNK1
Uniprot ID:: Q9HBU6
Molecular weight:: 27994.955

Reactions

Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolamine	details

Enzyme Details

5. Sphingosine-1-phosphate lyase 1

General function:: Involved in carboxy-lyase activity
Specific function:: Cleaves phosphorylated sphingoid bases (PSBs), such as sphingosine-1-phosphate, into fatty aldehydes and phosphoethanolamine. Elevates stress-induced ceramide production and apoptosis.
Gene Name:: SGPL1
Uniprot ID:: O95470
Molecular weight:: 63523.265

Reactions

Sphinganine 1-phosphate → O-Phosphoethanolamine + Palmitaldehyde	details
Sphingosine 1-phosphate → O-Phosphoethanolamine + Hexadecenal	details

Enzyme Details

6. Phosphoethanolamine/phosphocholine phosphatase

General function:: Involved in phosphatase activity
Specific function:: Phosphatase that has a high activity toward phosphoethanolamine (PEA) and phosphocholine (PCho). Involved in the generation of inorganic phosphate for bone mineralization.
Gene Name:: PHOSPHO1
Uniprot ID:: Q8TCT1
Molecular weight:: 32350.505

Reactions

O-Phosphoethanolamine + Water → Ethanolamine + Phosphate	details

Enzyme Details

7. Ethanolamine-phosphate phospho-lyase

General function:: Involved in transaminase activity
Specific function:: Catalyzes the pyridoxal-phosphate-dependent breakdown of phosphoethanolamine, converting it to ammonia, inorganic phosphate and acetaldehyde.
Gene Name:: AGXT2L1
Uniprot ID:: Q8TBG4
Molecular weight:: 55039.64

Reactions

O-Phosphoethanolamine + Water → Acetaldehyde + Ammonia + Phosphate	details

Enzyme Details

8. Ethanolamine kinase 2

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Highly specific for ethanolamine phosphorylation. Does not have choline kinase activity (By similarity).
Gene Name:: ETNK2
Uniprot ID:: Q9NVF9
Molecular weight:: 44781.125

Reactions

Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolamine	details

Enzyme Details

9. Ectonucleotide pyrophosphatase/phosphodiesterase family member 6

General function:: Involved in catalytic activity
Specific function:: Choline-specific glycerophosphodiester phosphodiesterase. The preferred substrate may be lysosphingomyelin (By similarity). Hydrolyzes lysophosphatidylcholine (LPC) to form monoacylglycerol and phosphorylcholine but not lysophosphatidic acid, showing it has a lysophospholipase C activity. Has a preference for LPC with short (12:0 and 14:0) or polyunsaturated (18:2 and 20:4) fatty acids. Also hydrolyzes glycerophosphorylcholine and sphingosylphosphorylcholine efficiently. Hydrolyzes the classical substrate for phospholipase C, p-nitrophenyl phosphorylcholine in vitro, while it does not hydrolyze the classical nucleotide phosphodiesterase substrate, p-nitrophenyl thymidine 5'-monophosphate. Does not hydrolyze diacyl phospholipids such as phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidylglycerol and phosphatidic acid.
Gene Name:: ENPP6
Uniprot ID:: Q6UWR7
Molecular weight:: 50240.625

Reactions

1-(1-Alkenyl)-sn-glycero-3-phosphoethanolamine + Water → 1-(1-Alkenyl)-sn-glycerol + O-Phosphoethanolamine	details

Enzyme Details

10. HRAS-like suppressor 2

General function:: Not Available
Specific function:: Exhibits PLA1/2 activity, catalyzing the calcium-independent hydrolysis of acyl groups in various phosphotidylcholines (PC) and phosphatidylethanolamine (PE). For most substrates, PLA1 activity is much higher than PLA2 activity. Catalyzes N-acylation of PE using both sn-1 and sn-2 palmitoyl groups of PC as acyl donor. Also catalyzes O-acylation converting lyso-PC into PC.
Gene Name:: HRASLS2
Uniprot ID:: Q9NWW9
Molecular weight:: 17393.695

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Phosphatidylcholine + O-Phosphoethanolamine → 1-acylglycerophosphocholine + N-palmitoyl-phosphoethanolamine	details

Showing metabocard for O-Phosphoethanolamine (HMDB0000224)

MOL for HMDB0000224 (O-Phosphoethanolamine)

3D MOL for HMDB0000224 (O-Phosphoethanolamine)

3D SDF for HMDB0000224 (O-Phosphoethanolamine)

3D-SDF for HMDB0000224 (O-Phosphoethanolamine)

PDB for HMDB0000224 (O-Phosphoethanolamine)

3D PDB for HMDB0000224 (O-Phosphoethanolamine)

SMILES for HMDB0000224 (O-Phosphoethanolamine)

INCHI for HMDB0000224 (O-Phosphoethanolamine)

Structure for HMDB0000224 (O-Phosphoethanolamine)

3D Structure for HMDB0000224 (O-Phosphoethanolamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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